ME02843B - Proces za masovnu proizvodnju monohidrata 1- [(2-bromofenil)sulfonil]-5-metoksi-3-[( 4- metil- 1-piperazinil)metil]-1h-indol dimezilata - Google Patents
Proces za masovnu proizvodnju monohidrata 1- [(2-bromofenil)sulfonil]-5-metoksi-3-[( 4- metil- 1-piperazinil)metil]-1h-indol dimezilataInfo
- Publication number
- ME02843B ME02843B MEP-2017-193A MEP2017193A ME02843B ME 02843 B ME02843 B ME 02843B ME P2017193 A MEP2017193 A ME P2017193A ME 02843 B ME02843 B ME 02843B
- Authority
- ME
- Montenegro
- Prior art keywords
- methyl
- hours
- formula
- piperazinyl
- methoxy
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Claims (12)
- 1. Postupak pogodan za proizvodnju velikih razmera 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1- piperazi-nil)metil]-1H-indol dimesilat monohidrata iz fornule (l), koja obuhvata:Korak (i): dovođenje u reakciju 1-metilpiperazina iz formule 1u prisustvu sirćetne kiseline i vodenog formaldehida iz formule l.na temperaturi u opsegu od 15 oC do 35oC tokom perioda od 1,5 sati do 2,5 sati da se dobije Manihov dodatak; Manihov dodatakKorak (ii): dovođenje u reakciju Manihovog dodatka sa 5-metoksiindolom iz formuleu prisustvu metanola na temperaturi u opsegu od 15 oc do 40 oc tokom perioda od 2,5 sata do 3,5 sata da se dobije 5-metoksi-3-[(4-metil-1-piperazinil) metii]-1H-indol iz formule 4;Korak (iii): kristalizacija 5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indol iz formule 4 u toluenu zagrevanjem rastvara do 85 oC - 95 oC tokom perioda od 1 sat, posle čega sledi hlađenje rastvara do 1O oC - 15 oC tokom perioda od 3 sata;Korak (iv): rekristalizacija 5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indola iz formule 4 u toluenu zagrevanjem rastvara do 95 oC - 105 oC tokom perioda od 2 sata, posle čega sledi hlađenjej rastvara do 1O oC -15 oC tokom perioda od 3 sata;Korak (v): dovođenje u reakciju gore dobijenog cristalnog 5-metokis-3-[(4-metil-1-piperazinil)metil]-1H-indola iz formule 4 sa 2-bromobenzensulfonil hloridom iz formule 5 ;u prisustvu tetrahidrofurana i kalijum hidroksida na temperaturi u opsegu od 20 oC do 40 oC na period od 3,5 sata do 4,5 sata da se dobije 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indola iz formule 6;Korak (vi): pretvaranje 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indola iz formule 6 u prisustvu etanola i metansulfonske kiseline na temperaturi u opsegu od 15 oC do 35 oC na period od 18 sati do 24 sata da se dobije 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indol dimezilata iz formule 7;Korak (vii): pretvaranje 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indol dimezilata iz formule 7 u prisustvu kašaste materije vodenog etanola i ugljenika na temperaturi u opsegu od 75 oC do 85 oC na period od 0,5 sata - 1,5 sat da se dobije 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil- 1-piperazinil)metil]-1H-indol dimezilat monohidrata iz formule (l).
- 2. Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je temperatura korišćena u Koraku (i) 20 OC do 30OC .
- 3. Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je trajanje reakcije u Koraku (i) 2 sata.
- 4. Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je temperatura korišćena u Koraku (i) 20 OC do 35 OC.
- 5. Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je trajanje reakcije u Koraku (i) 3 sata.
- 6. Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je temperatura korišćena u Koraku (v) 25 OC do 35 OC.
- 7 Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je trajanje reakcije u Koraku (v) 4 sata.
- 8. Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je temperatura korišćena u Koraku (vi) 25 OC do 30 OC.
- 9. Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je trajanje reakcije u Koraku (vi) 24 sata.
- 10. Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je temperatura korišćena u Koraku (vii) 75 °C do 80 °C.
- 11. Postupak za koji se zaštita traži u patentnom zahtevu 1, pri čemu je trajanje reakcije u Koraku (vii) 45 minuta.
- 12. Postupak za koji se zaštita patentom traži u patentnom zahtevu 1, pri čemu je čistoća 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1- piperazinil)metil]-1H-indol dimezilat monohidrata veća od 99 %.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14725245.6A EP3077375B1 (en) | 2013-12-02 | 2014-02-20 | Process for large scale production of 1-[(2-bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1h-indole dimesylate monohydrate |
| IN5537CH2013 IN2013CH05537A (me) | 2013-12-02 | 2014-02-20 | |
| PCT/IN2014/000109 WO2015083179A1 (en) | 2013-12-02 | 2014-02-20 | Process for large scale production of 1-[(2-bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1h-indole dimesylate monohydrate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02843B true ME02843B (me) | 2018-01-20 |
Family
ID=54199404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2017-193A ME02843B (me) | 2013-12-02 | 2014-02-20 | Proces za masovnu proizvodnju monohidrata 1- [(2-bromofenil)sulfonil]-5-metoksi-3-[( 4- metil- 1-piperazinil)metil]-1h-indol dimezilata |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US9540321B2 (me) |
| EP (1) | EP3077375B1 (me) |
| JP (1) | JP6151453B2 (me) |
| KR (1) | KR101808792B1 (me) |
| CN (1) | CN105814020B (me) |
| AP (1) | AP2016009224A0 (me) |
| AU (1) | AU2014358682B2 (me) |
| BR (1) | BR112016010788B1 (me) |
| CA (1) | CA2929309C (me) |
| CY (1) | CY1119298T1 (me) |
| DK (1) | DK3077375T3 (me) |
| EA (1) | EA028038B1 (me) |
| ES (1) | ES2638856T3 (me) |
| HR (1) | HRP20171245T1 (me) |
| HU (1) | HUE036008T2 (me) |
| IL (1) | IL245619B (me) |
| IN (1) | IN2013CH05537A (me) |
| LT (1) | LT3077375T (me) |
| ME (1) | ME02843B (me) |
| MX (1) | MX364930B (me) |
| NZ (1) | NZ719671A (me) |
| PL (1) | PL3077375T3 (me) |
| PT (1) | PT3077375T (me) |
| RS (1) | RS56323B1 (me) |
| SI (1) | SI3077375T1 (me) |
| SM (1) | SMT201700408T1 (me) |
| WO (1) | WO2015083179A1 (me) |
| ZA (1) | ZA201602954B (me) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ748280A (en) * | 2016-05-18 | 2020-07-31 | Suven Life Sciences Ltd | Combination of pure 5-ht6 receptor antagonists with acetylcholinesterase inhibitors |
| SG11201809725TA (en) * | 2016-05-18 | 2018-12-28 | Suven Life Sciences Ltd | Combination of pure 5-ht6 receptor antagonists with nmda receptor antagonist |
| KR102016120B1 (ko) | 2016-05-18 | 2019-10-21 | 수벤 라이프 사이언시스 리미티드 | 순수한 5-ht6 수용체 길항제, 아세틸콜린에스테라제 저해제 및 nmda 수용체 길항제의 3중 조합물 |
| RS62113B1 (sr) * | 2016-10-03 | 2021-08-31 | Suven Life Sciences Ltd | Farmaceutske kompozicije antagoniste 5-ht6 |
| IL271694B2 (en) * | 2017-07-03 | 2025-01-01 | Suven Life Sciences Ltd | New uses of a pure 5-HT6 receptor antagonist – the compound 1-[(2-bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1-hydrogen-indole or its pharmaceutically acceptable salts |
| US20220409614A1 (en) | 2019-12-02 | 2022-12-29 | Suven Life Sciences Limited | Treating behavioral and psychological symptoms in dementia patients |
| MA57828B1 (fr) | 2019-12-02 | 2025-09-30 | Suven Life Sciences Limited | Combinaisons du masupirdine avec du donépézil ou de la mémantine pour le traitement de symptômes comportementaux et psychologiques chez des patients atteints de démence |
| CN111362859B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
| CN111233737B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
| CN111362858B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
| CN117567449A (zh) | 2020-10-13 | 2024-02-20 | 勃林格殷格翰国际有限公司 | 再加工方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2749846B1 (fr) * | 1996-06-17 | 1998-09-11 | Pf Medicament | Sel de methanesulfonate d'une arylpiperazine derivee de tryptamine et ses solvates pour usage pharmaceutique |
| US7875605B2 (en) | 2002-11-28 | 2011-01-25 | Suven Life Sciences Limited | N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them |
| SI1581538T1 (sl) * | 2002-12-18 | 2007-08-31 | Suven Life Sciences Ltd | Tetraciklični 3-substituirani indoli z afiniteto za receptor serotonina |
| RU2008151724A (ru) * | 2006-06-12 | 2010-07-20 | Новартис АГ (CH) | Способ получения солей n-гидрокси-3-[4-[[[2-(2-метил-1н-индол-3-ил)этил]амино]метил]фенил]-2е-2-пропенамида |
-
2014
- 2014-02-20 AU AU2014358682A patent/AU2014358682B2/en active Active
- 2014-02-20 AP AP2016009224A patent/AP2016009224A0/en unknown
- 2014-02-20 CA CA2929309A patent/CA2929309C/en active Active
- 2014-02-20 PT PT147252456T patent/PT3077375T/pt unknown
- 2014-02-20 SI SI201430348T patent/SI3077375T1/sl unknown
- 2014-02-20 HR HRP20171245TT patent/HRP20171245T1/hr unknown
- 2014-02-20 IN IN5537CH2013 patent/IN2013CH05537A/en unknown
- 2014-02-20 CN CN201480065601.9A patent/CN105814020B/zh active Active
- 2014-02-20 PL PL14725245T patent/PL3077375T3/pl unknown
- 2014-02-20 DK DK14725245.6T patent/DK3077375T3/en active
- 2014-02-20 HU HUE14725245A patent/HUE036008T2/hu unknown
- 2014-02-20 EP EP14725245.6A patent/EP3077375B1/en active Active
- 2014-02-20 US US15/100,489 patent/US9540321B2/en active Active
- 2014-02-20 WO PCT/IN2014/000109 patent/WO2015083179A1/en not_active Ceased
- 2014-02-20 KR KR1020167013965A patent/KR101808792B1/ko active Active
- 2014-02-20 EA EA201691161A patent/EA028038B1/ru unknown
- 2014-02-20 ME MEP-2017-193A patent/ME02843B/me unknown
- 2014-02-20 NZ NZ719671A patent/NZ719671A/en unknown
- 2014-02-20 RS RS20170853A patent/RS56323B1/sr unknown
- 2014-02-20 MX MX2016006629A patent/MX364930B/es active IP Right Grant
- 2014-02-20 LT LTEP14725245.6T patent/LT3077375T/lt unknown
- 2014-02-20 JP JP2016535680A patent/JP6151453B2/ja active Active
- 2014-02-20 ES ES14725245.6T patent/ES2638856T3/es active Active
- 2014-02-20 BR BR112016010788-8A patent/BR112016010788B1/pt active IP Right Grant
- 2014-02-20 SM SM20170408T patent/SMT201700408T1/it unknown
-
2016
- 2016-05-03 ZA ZA2016/02954A patent/ZA201602954B/en unknown
- 2016-05-11 IL IL245619A patent/IL245619B/en active IP Right Grant
-
2017
- 2017-08-28 CY CY20171100904T patent/CY1119298T1/el unknown
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